Richard Haig is a remarkably intelligent, charming, ageing poetry professor, whose life away from the classroom at Cambridge is one of constant hedonism and an unquenchable lust for women. He thinks nothing of sleeping with his attractive grad student Kate and even shamelessly makes a move on her hardlined older sister Olivia, much to her displeasure. Richard is forced to confront the consequences of his over-indulgent behaviour when Kate announces she's pregnant with his child. While fatherhood has never appealed to him much, he is ready to settle down, get married and experience family life, but when Kate falls in love with somebody else, it becomes clear that he's still got a long way to go before he can be considered a responsible person. Kate allows their son to stay with Richard, but only under the supervision of Olivia, who's about to teach Richard more about life and romance than he's ever taught about poetry.

Playing Mona Lisa follows the life of Claire Goldstein (Alicia Witt), who slowly unravels as various forces of nature turn against her. Claire's life is not unlike the movie as a whole, which starts off strong but meanders to a non-ending that is unlikely to leave anyone very satisfied.

Claire is a "brilliant" 23-year old pianist, which is apt casting for Witt, considering she is also a real-life piano prodigy. On the eve of her graduation from the San Francisco Academy of Music, Claire's life starts to come undone. First she doesn't make it into a big piano competition. Then she gets dumped, then evicted, then just plain whiny as she realizes her family (with whom she is now forced to live) is full of freaks.

Claire Goldstein is all giddy and aglow because last night her wonderful, wonderful boyfriend asked for her hand in marriage. Unfortunately it's morning now, he's sober, and not only has be blacked out popping the question, but he's also started thinking maybe they shouldn't see each other anymore.

That's only the beginning of Claire's problems in "Playing Mona Lisa," a breakup recovery screwball comedy that in many marvelous ways invokes the spirit of Woody Allen -- if Woody Allen were a comely, quizzical, capriciously miserable 23-year-old redhead from San Francisco.

Trying to withdraw from the world by staying in bed and eating Ho-Hos by the boxful, poor Claire (the comically gifted Alicia Witt) can't even wallow in self-pity to her satisfaction because her busybody family keeps showing up to chicken-soup her heart with useless anecdotes and unsolicited advice.